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5 Best Places To Visit During The Holidays In New England

5 Best Places To Visit During The Holidays In New England

Happy holidays fam! Since 2020 has brought me back to Boston for the year, I’ve been doing a lot more local travel than I ever anticipated doing. I’ve explored more of New England in these past few months than I have my whole life- and I really can’t complain. It’s been amazing getting to know my area more. I’m so lucky to live at the crossroads of beaches, mountains, cities, and SIX states to explore. I’ve written several posts about New England this year, including my Ultimate New England Bucket List, which I update often, and my fall-themed Leaf Peeping post. Today’s post is going to cover the five best places to visit during the holidays in New England!

Go Here During the Holidays in New England

1. Kennebunkport, Maine

Most people think the southern coast of Maine has its shining moments during the summer months, but Kennebunkport NEEDS to be on your winter bucket list!

Each December, Kennebunkport hosts its annual Christmas Prelude, a two week festival with special events, festive decor, shopping sales, and happy hour deals. If you visit, I recommend dining at Allison’s for dinner (you need to try their lobster bisque). Check out the gondolas and igloos at the Kennebunkport Inn for drinks or dinner. There’s also an outdoor Christmas market located across the street from the Old Vines Wine Bar!

Each December there’s an event held called “It’s a Nutty Christmas” which is basically a holiday-themed scavenger hunt where visitors try to find the 60+ hand-painted nutcrackers hidden throughout the town! How cute!

Downtown Kennebunkport decked out for the holidays in New England
Downtown Kennebunkport decked out for the holidays
The Kennebunkport Inn during the holidays in New England
The Kennebunkport Inn
Igloo dining at the Kennebunkport Inn during the holidays in New England
Igloo dining at the Kennebunkport Inn

2. Newport, Rhode Island

Newport is the perfect day or weekend trip year-around. In the summer months you can walk the 3-mile long coastal Cliff Walk, visit the aquarium, and browse the shops downtown. However, I think December is when Newport’s crown jewels come to life… the Newport Mansions!

Each December, the two most famous Newport Mansions, the Breakers and the Elms, are decked out floor to ceiling in the most stunning Christmas decor. This year because of COVID, some attractions are outside of the homes, meaning there’s double the holiday decor! If you’re looking for a festive activity to put you in the holiday spirit or to snap some festive pics, check out Newport!

Pro-tip: You can buy tickets to take self-guided tours of the homes here!

3. Boston, Massachusetts

Boston has to be on this list! Known for it’s cold, snowy, winter weather, Boston’s holiday charm really comes to life each December. As a local, I recommend enjoying the holiday decor on a holiday trolley ride! I did the Lights & Sights tour last year and really enjoyed it. I also recommend visiting Faneuil Hall, which gets decorated beautifully each year. The main attraction is the Blink! Light and Sound Extravaganza, which is basically a giant Christmas tree that has a light show coordinated with music each hour. Unfortunately because of COVID, the tree won’t be going up in 2020, but there is a smaller one in the Boston Common!

Another holiday activity I recommend in Boston is the Nutcracker! Boston Ballet’s Nutcracker is one of the best holiday performances in the city. It’s been performed for decades and is really well done. The Boston Pops also put on a wonderful holiday show each year.

Ice-skating at Frog Pond is also a super fun festive activity. I love coming here at nighttime when the city lights shine bright and the Common is decked out in Christmas lights.

Lastly, if you have kids, you HAVE to go see Disney on Ice at the TD Garden. This was the highlight of my childhood.

Last year in Faneuil Hall with Nathaniel
Last year in Faneuil Hall with Nathaniel

4. Portsmouth, New Hampshire

Portsmouth is one of the most festive towns in New England. It’s actually known as one of the world’s Christmas capitals! Each December the city of Portsmouth has a tree lighting event and parade. The tree lighting takes place right in Market Square, where the tree is put up each year. The parade was canceled this year because of COVID, but the town is still decked out the the max!

This year the Portsmouth Historical Society is celebrating its 30th annual Gingerbread House Exhibit and Contest! The storefronts in Market Square all have the gingerbread houses on display in their windows. And these aren’t just your typical gingerbread houses, there are mansions, tree houses, etc. Check them out!

Portsmouth also has several holiday events each year including the annual Candlelight Stroll Under the Stars at Strawberry Banke! This is self-guided and completely COVID safe since it’s all outdoors and tickets are sold to limited groups each hour. There’s also an ice skating rink at Strawberry Banke!

My last recommendation is to visit Wentworth by the Sea, the seacoast’s most historic hotel. There’s a giant (and I mean giant) gingerbread house on display here and it’s decorated beautiful for the holidays. The lobby is so cozy and is the perfect place to grab a Christmas cocktail!

Pro-tip: Want to see it all? Portsmouth has a holiday trolley too! I did this a few years ago with Nathaniel’s family and had a blast.

Market Square decorated for Christmas
Market Square decorated for Christmas
Gingerbread buoy shack
Gingerbread treehouse
Inside the Wentworth by the Sea hotel with Nathaniel
Inside the Wentworth by the Sea hotel with Nathaniel

5. Woodstock, Vermont

Woodstock, VT was on my fall leaf peeping bucket list, but wow, this place HAS to be on the holiday list too! This town is one of the most charming towns in New England and truly comes to life around the holidays. The town square is lit up with twinkling lights, the covered bridge is decorated, and don’t even get me started on the Woodstock Inn. This places brings cozy to a whole new level.

You should visit Woodstock during the Wassail Weekend, where the town celebrates the opening of the holiday season with a horse-drawn carriage parade in costume, historic home visits, caroling, concerts, food, wassail and good cheer throughout!

Pro-tip: This weekend is normally the first weekend of December.

One of my favorite things about the holidays in New England...Woodstock's famous covered bridge
Woodstock’s famous covered bridge
The lobby of the Woodstock Inn during the holidays in New England
The lobby of the Woodstock Inn

Ok, I promised this list would be the top 5 places to visit in New England during the holidays, but if you made it this far, I have a surprise for you! Here’s a 6th recommendation for the holidays in New England: It’s the Yankee Candle Village in Deerfield, MA! Known as one of New England’s favorite day trip destinations, you can personalize candles to capture cherished memories in scents and wax, catch snowflakes indoors at the Bavarian Village, satisfy your sweet tooth, shop for toys, gifts, home décor, and kitchen and garden items, and celebrate Christmas every day!

I hope these ideas inspire you to enjoy the holidays in New England, whether it be this year (with your mask on of course) or in years to come! Happy holidays everyone!

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  1. Gustavo Morales Ramírez December 10, 2020 / 11:30 PM

    We had the Freedom walk trail with Nicole earlier today, and I loved it. We arrived late and she wasn’t mad at all, she is very intelligent and well prepared. And she was also really nice to me. She is really dedicated and she even has her own professional website, that’s admirable. I can tell traveling is her passion but she helps tourists to get to know Boston and 20 other places. I’m really thankful and I can tell that creating your own website must have required a lot of hours and effort, but if every costumer of yours, end up as happy as I did, you’ll get really far. (As you are already). I’d love to take another of her tours before I leave.
    Also she speaks so loud and clear, flawless.

  2. Nicole Rosania December 14, 2020 / 12:56 AM

    Thank you so much for your kind message!I loved having you on my tour!

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